4-Chloroaniline → HCID 66927432, compound

Participants

Reaction Steps

A mixture of N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-2,2-dimethylpropyl)-4-bromobenzamide 120 as a white solid (2.38 mmol), 4-chloroaniline (0.64 g, 5.0 mmol), and K2CO3 (1 g, 7.23 mmol) in methanol (20 mL) and THF (2 mL) was stirred for 18 h at room temperature. The reaction was quenched with 2M HCl and extracted with ether. The organic solution was concentrated onto silica gel and chromatography (9:1 hexanes:ethyl acetate) and gave 4-bromo-N-(1-methoxy-2,2-dimethylpropyl)benzamide and the title product. The product was titrated with ether to give pure 4-bromo-N-(1-(4-chlorophenylamino)-2,2-dimethylpropyl)benzamide (Compound-38) (104 mg, 11%). 1H NMR (300 MHz, d6-DMSO): δ=8.34 (d, J=8.4 Hz, 1H), 7.76 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H), 6.71 (J=8.7 Hz, 2H), 5.81 (d, J=6.6 Hz, 1H), 5.19 (t, J=3.9 Hz, 1H), 1.03 (s, 9H).

Provenance & Evidence